Dichloromethane → 5-Bromo-2-(bromomethyl)pyrimidine

HRID 712231노트

반응식

HRID 712231 반응식
[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1.CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:28])C(=O)C1.C(Cl)Cl>C(Cl)(Cl)(Cl)Cl.CCCCCC>[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH2:8][Br:28])=[N:6][CH:7]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 143877445-Bromo-2-methylpyrimidine

생성물 1

HCID 205577975-Bromo-2-(bromomethyl)pyrimidine수율 25.5%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 8058Hexane용매

반응 조건

온도
70 °C

실험 절차

To an ice-cold solution of 5-bromo-2-methylpyrimidine (3.5 g, 20.23 mmol) in CCl4 (20 mL) was added AIBN (0.14 g, 2.02 mmol) followed by portion wise addition of NBS (3.6 g, 20.23 mmol) and the mixture stirred at 70° C. for 30 h. After completion of reaction (by TLC), DCM (150 mL) was added and washed with water and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 2% EtOAc:hexane to obtain the desired product (1.30 g, 25% yield). 1H NMR (CDCl3): δ 4.68 (s, 2H) and 9.03 (s, 2H).

후처리

  1. additionwas added
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified over 100-200 M silica-gel

출처 및 근거

ORD 기록
ord-06da0a75b61d4a688cbd2e19bc5f5d7f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181234B2

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